The boards used are generally smaller than actual surfboards, and look more like snowboards or large skateboards. The attachment to the feet is normally made removable, so that if the skydiver loses control or has difficulty opening their parachute, the board can be jettisoned. Surf Flite was the first sky board company, copyrighted by Jerry Loftis (January 1, 1969 – August 12, 1998).

Skysurfing is a skill requiring considerable practice. The simplest skysurfing technique is to stand upright on the board during freefall, and tilt the nose of the board down to generate forward movement. However even this basic technique is a balancing act which experienced skydivers find tricky to learn. The extra drag of the board tends to upset the balance and make the skydiver flip over. The jumper must also learn to control the board and their body position so as to open the parachute in a stable configuration. More advanced aerobatics such as loops, rolls and helicopter spins, are more difficult still and are tackled once the basics have been mastered. Since some techniques require constant spinning at a high speed, one technique some skysurfers take to is tightly wrapping ace bandages all the way up the arms and legs to keep the blood from pooling at the end of your limbs. Even with the bandage technique, however, many techniques in skysurfing can be extremely painful.

Because of the possibility of dropping the board, not every skydiving club permits skysurfing, and only a minority of skydivers have attempted this recent specialisation in the sport.

When a skysurfer is filmed by another skydiver falling alongside them, the resulting film gives the appearance that the skysurfer is riding on the air in the same way a surfer rides on a wave. The downward motion is not very apparent and this creates the illusion that a skysurfer is gliding on air currents like a sailplane or hang glider. In fact a skysurfer always falls at a high speed comparable to any other freefalling parachutist. The competitive discipline of skysurfing is a team sport consisting of a skysurfer and a camera flyer with a video camera.

The Sky Surf was invented by two French skydivers, Dominique Jacquet and Jean-Pascal Oron in 1986 but it became popular and gained recognition during the 1990s thanks to the efforts of the first few exponents to master the more complex aerobatics, such as the late Patrick de Gayardon and the late Jerry Loftis. The rise of skysurfing coincided with other new-age disciplines in skydiving, such as freestyle and freeflying. Freestyle skydiving is a balletic, mostly individual style which seeks to extend the sport beyond the traditional belly-to-earth flat position used by most skydivers who make formations with their bodies.

Freeflying is also a form of skydiving using a variety of body positions, such as head-down or feet-to-earth, while still building formations with others. These evolutions in skydiving have taken the sport further away from the traditional image of a daredevil stunt.

Skysurfing reached its peak in popularity in the late 1990s. Skysurfers were featured in prime time television commercials for major brands like Pepsi and AT&T. Competitive team skysurfing was featured as part of the ESPNX Games from 1995 to 2000. In 1996 and 1997, the SSI Pro Tour staged eight X-Trials qualifying events in both North America and Europe. During this six-year period, pro skysurf teams received a total of $392,000 in cash winnings and the discipline garnered over 100 hours of global TV exposure without incident. After ESPN decided not to renew the sport for the seventh season, skysurfing has become relatively rare in the skydiving community. Reasons for the decline include the rise in popularity of freeflying and wingsuit flying, the hazards associated with flying and releasing the board, and the dwindling number of experienced skysurfers to train new pilots.